


Pretty Boy

by saviorbrother



Category: Supernatural
Genre: M/M
Language: English
Status: Completed
Published: 2015-09-04
Updated: 2015-09-04
Packaged: 2018-04-19 01:03:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,374
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4726916
Author URL: https://archiveofourown.org/users/saviorbrother/pseuds/saviorbrother
Summary: <blockquote class="userstuff">
              <p>Sam does four years at Stanford</p>
            </blockquote>





	Pretty Boy

Sam does four years at Stanford before deciding that it just doesn't feel right. His parents supported his decision, Bobby and Jody moved over to New York after Bobby got a job at one of the precinct's in Manhattan. Now, Sam went through all the works and at 25, he's ready.

"Come to the city, you said. It'd be great you said," Sam mutters under his breath at his father as they walk through the precinct to get to the chief.

His shoes are wet and so are his black pants.

"Shut up, it rains sometimes, so what?" Bobby rolls his eyes and takes off his coat.

"It wasn't in the forecast! And that train was like a zoo," Sam huffs.

Bobby mutters to himself as he knocks at the glass window of the door.

John Winchester, Commander in Chief 

Sam turns to look around the bustling office as they wait. Papers never stop shuffling and people never stop moving. Some officers are dressed down and some are in uniform, he's just hoping he'll be able to dress in his regular suit.

"Sam Campbell," a smooth voice breaks his concentration as he whirls back around.

"Uh, Mr. Winchester," Sam stutters and puts out his hand for John to take it.

"Come on in, I've been waiting for you," the man smiles.

He looks younger than Sam expected. Beard going just a tad bit grey, lines around his mouth, and shorter than him. He's comfortable immediately.

\--

He had the job before he even landed in the city, apparently. He got a finger of whiskey for his trouble, sweaty and nervous. He doesn't have to do much, dress in suit if he wants, dress in regular clothes if he feels like it. 

"You've got it all easy, kid. Your daddy here has been a long time friend of mine and the academy had some good things to say," John nods as Sam and Bobby stand back outside his office.

"Yessir," Sam answers, palms clammy.

John looks over his shoulder, "Castiel! Come meet your new partner!"

The guy is 5'11 of blue eyes and dry humor, Sam finds.

"Pull my finger," Cas asks with a small smile.

Sam scoffs in amusement from his perch on his partner's metal desk. He's like a baby in a trench coat.

\--

He meets the devil on a Tuesday, a week from his first day. Sam had heard about Dean Winchester here and there around the way. On the block from a few druggies or prostitutes they picked up on the night shift. He doesn't know much except that he's the boss's kid.

Sam is leaning on John's desk with a bottle of water in hand, Bobby sitting in the chair across from his friend when Dean walks in.

"Dad, you know you should--and who is this?"Dean Winchester, man of the year, asks.

It's slow tonight, running on a skeleton crew cause they don't get a lot on the beat so early in the week. This man, his boss's son, is magnificent. Sam pushes a couple stray hairs out of his eyes and his dry throat clicks as Dean comes to stand in front of him. Dressed in a charcoal grey suit, black tie, and the shiniest leather shoes Sam has ever seen. 

"S-sam Campbell," he answers, his eyes flit from John to Dean.

"Why d'ya look so scared, boy?" Bobby barks at him, loosening the blue tie he has on.

Sam isn't scared, he's nervous. Flustered. Shy.

"Nice to meet you, Sam. I'm Dean," a large hand takes his gently as green eyes bore into his.

He can barely keep himself from flushing before he's excusing himself out the room and tripping over himself. He's a clumsy asshole and that was no way to make an introduction with him. Sam is sure Dean isn't an officer or detective, he wold have seen him around the precinct. Maybe a lawyer with that fitted suit he was wearing.

\--

"Mob what?" Sam coughs up part of his sandwich when Cas tells him over lunch. He looks around the empty diner.

It's one in the afternoon on Sunday.

"Mob boss? Like the ones on the TV?" Castiel shrugs while picking apart his salad.

"Yeah, I know," he answers and wipes at his mouth, "but isn't his father one of the most respected chief's in the city?" 

Castiel raises his head in confusion, furrowing his eyebrows.

"Yes. All the better. John and all the boys at the station can cover for Dean when he needs it. He also gives good cuts to everyone. Dean is not a bad guy, at all."

"So he gets away with everything that he does," Sam sneers.

It's the first time he's seen Castiel show an emotion as close to dangerous as he can get.

"Are you gonna do something about it?"

Sam flounders for a second, "Uh--I guess not?"

"Good. Cause something would have been done about you," Castiel smiles.

Sam takes a sip of his water after some silence, his partner seems unbothered as the waitress comes over to refill his cup of coffee. 

"Pull my finger!"

\--

Sam gets it now. It's all one big family in this corrupt city. No, he hasn't seen Dean actually kill anyone or sell any drugs, or even disrespect anyone. He's down to earth and...normal. Sam sees him a bunch more around. More often than not he can feel the man's gaze following his ass when he walks past or catching his eye when Sam looks up as he walks in.

"Sammy, working hard?" Dean sits on his desk as he tries to get paper work done on a hooker.

He pushes his hair back and purses his lips.

"Yes, trying to get some done, thanks for asking," he snarks as he types away.

The girl sitting in the chair to his left looks between the two of them.

"Dean, leave him alone so he can book me. I'm fucking tired," she, Amy, says.

"Long night?" Dean smiles at her, crows feet beautiful.

"Yeah. Violent guy," she sighs, looks down at her busted knees.

Sam feels some guilt for locking her up, but it's his job.

"Want me to handle him, Amy?" Dean asks softly.

Sam turns to him in surprise. His eyes soft and searching on her face. Sure, Dean is laid back, easy going guy as far as Sam knows, but he never pegged him for the sympathetic type.

"I know you've got the kid at home. I could get you a job at the bakery on 96th and 2nd," Dean whispers.

Once Amy starts to cry, Sam deletes the whole report, even without Dean's look over his shoulder. It's the first time Sam starts to feel something other than lust for the man.

\--

It's just a coincidence that Sam starts wearing his slacks tighter and matching his shirt and tie. He makes sure his hair is right and that he applies a soft cologne liberally. His roommate, Jess, tells him he looks good everyday before he leaves. He likes to look hot sometimes, he's learned that to feel good about himself, he needs to look the way he wants. He also wants to get laid.

"Sam, Sam, Sam, hiding that great ass for three weeks?" Pamela teases him as he walks into the bar after his shift.

Bobby and John laugh from behind him as Sam burns up. Dean is watching him from beside her. This time dressed in just a white shirt and black slacks. 

"Could bounce a nickle off that thing," she purrs to Dean as Sam pays for a beer.

He hears Dean give a rumbling affirmation. 

"Finally taking a load off, pretty boy?" he hears to his right.

Dean is one of the tallest guys he knows. Sam is taller, but Dean is one guy that could take him. Bulging muscles in that dress shirt, not too much, but enough that Sam knows he holds power.

"It's Friday night, I needed a break," Sam smirks over at him, tries to play it cool.

"I could help you take a load off, baby boy," Dean takes a sip of beer right after.

Sam stares at Dean in shock, music and laughing go on around them. Dean's look is suggestive, but holds no pressure.

"The offer is always on the table. I won't force you into anything. I know you know what I do. I know you don't really respect it. Lawful boy like you likes his justice, but I'm not a bad guy, Sammy," Dean talks to him quietly, eye to eye.

Sam frowns because Dean is right. He has this job to uphold the law, but here he is fawning over this crime boss. Sure, he's the nicest one he's ever heard of, and discreet, but that doesn't excuse anything.

"Lawful boys like me don't get into anything with bad men like you," Sam leans in close enough to feel Dean's breath on his lips, "even though you're very tempting."

His lips ache with the want to press into that mouth. When he meets Dean's gaze, that knowing gaze, Sam leaves is beer on the bar and dashes out into the crisp night air.

Sam is a lawful man, he will uphold the law. Sam is a lawful man. Sam believes in justice. Sam interrupts the corrupt and brings them in. He should not befriend those who defend the unjust and those who benefit from them. He should not be infatuated with the man at the head of it all, he should be telling others about how Dean Winchester runs the streets, how he probably has his goons throw people in rivers, and how he sells drugs. He doesn't have solid evidence on him, but that's what mob bosses do, right? All he's seen is Dean help out women selling their bodies, give money to charities, give back to kids in poverty, and treat everyone with respect.

Sam practically sprints back to the apartment to spill to Jess, ask her if he's doing the right thing. Ask her exactly what is he doing if he isn't upholding the law? What is any officer in that precinct doing if they aren't defending the justice system?

"I think Dean is justice. Sounds to me like he does more good than bad," Jess tells him, sitting down on their worn couch.

Her blonde curls fall around her shoulders as she eyes him with pity.

"What's the point of this job? And he's a good guy, what crime lord is a nice guy?" Sam murmurs.

"I don't know. You should give him a chance, though. I mean, you could live a great life. Rich and I bet he'd spoil your ass rotten," Jess giggles.

"Whatever."

\--

Sam sees Dean each day at the office and the local bar. They talk for longer each day and sometimes Sam comes in to find a note and gummy worms sitting on his desk. He caught a hissy fit the first time he found a rose and got teased all day long about it. He shares them when Dean passes by and sits on the edge of his desk every morning.

"Metallica or Led Zeppelin?"

"Gummy bears or Gummy worms?"

"Pie or cake. So help me God if you say cake!"

"Burger or salad?"

They get to know each other better, Dean walks beside him when everyone goes to the bar. Dean buys him a drink and they both loosen their ties. He walks Sam to the train and doesn't ever pressure him to take Dean's offer for a ride home.

On the third Monday, Sam walks in to find a piece of apple pie sitting fresh and warm on top of his folders. 

Apple pie for the apple of my eye. My pretty boy-- D

"He's so into you it's sickening," John says from behind him.

"I--uh, sir-"

"Call me John, kid," the older man sighs.

He sees Castiel skid to a stop a few feet away.

"My boy is a good one. I know you've got your hang ups about him, but give him a chance," John advises.

He utters out a 'yessir' as John walks away towards his office. He wore his gray shirt and purple tie today, and a pair of gray slacks that accentuate his legs. He might have sweat through his shirt.

"Hey, sweetheart. You gonna enjoy the pie or stand there all day," Dean exclaims.

Sam twists around to see him dressed in a pair of jeans and a black t-shirt, leather jacket in hand.

"Yeah, asshole. Could you let me get situated first?" he smiles.

"Anyway, beers or liquor tonight?" Dean has a slight bruise under his right eye, but Sam has learned not to ask about those.

"Beer, definitely."

"Good, now lemme see those sweet lips wrapped around that fork."

\--

He gets taken out to a small bar, one of Dean's personal dives.

"I like to drink here when I need my own space," he says, his voice relaxed.

It's almost dark in here, one table in the corner where Dean's guards are sitting and five bar stools are all that are in this place. It's intimate, Sam doesn't mind it.

Dean places a hot hand on Sam's lower back every so often when a friend comes in and says hello, introducing him. Or he has Dean leaning in close to whisper to him, a hand on his, and one squeezes his knee. That touch makes Sam chub up in his pants so he has to push his thighs together to ease the ache.

"It's already two, I gotta work in the morning," Sam twirls his empty beer around on the wooden surface of the bar, neon light glimmering onto it.

They're huddled close, knees pressing tightly, fingers twined together on Dean's lap, and their faces inches apart.

"Then let me walk you home tonight, Sammy," Dean's voice has a begging tone to it, more concerned about him being safe.

He thinks about it for just a second and nods, standing up and let's Dean grab his jacket.

They say goodnight to Donny and walk out into the cool air of New York. As he waits for Dean to shrug on his jacket, two men cross the street quickly.

"Dean, watch it," he growls.

He gets a curious look but instantly recognizes one of the guys with a scowl.

"Benny? What are you doing here?" Dean grinds out between his teeth.

"You know already, brother," the blonde man hisses, lunging at Dean.

Sam let's Dean fight it out, throwing swift punches at Benny? Who the fuck is Benny anyway? A fist connects nastily in the guys face, bone crunching. Dean's mouth is bleeding when he lays the second guy out on his back.

"Okay, that's enough, we need to go," Sam grips him by the arm and pulls him forcefully away from the two trying to get back up.

\--

"Guess that didn't raise the bar none," Dean croaks, sitting in the plastic chair.

Sam sets his mouth in a firm line, scooting to the edge of the rickety table to finish cleaning the corner of Dean's bust lip.

The light in the kitchen buzzes as Sam thinks about an answer.

"Why'd he fight you?" he asks, leaning back to dab the cloth in more hot water.

"Truth?" Dean closes his eyes, dreading it.

Sam tilts his head to the side, cupping the face in front of him, "Yeah."

"A friend of his was killed. By one of mine last week. It was an accident," Dean searches Sam's face as he speaks.

Sam likes the way they dilate in the light, makes Sam feel like some natural wonder of the world. 

"It was supposed to be a raid. His friend had stolen some merchandise that was gonna be auctioned off for charity in a few days. Went to go get it back and it turned into chaos inside the warehouse."

"How come the precinct didn't hear about this?" Sam asks.

"Dad and Bobby know. It happened in Brooklyn, though. So," Dean finishes, tearing his eyes away.

Sam looks over at the dark living room and remembers what Jess said about Dean.

"I don't think any less of you. You're suppose to be this crime or mob boss, but you're not, really," Sam sighs.

"Not all the time. I do bad things, I've done shit I ain't proud of. Who hasn't? I try to keep a balance in what I do."

"I've never really gotten a negative vibe from you. You're a good person, Dean,"Sam states and Dean lifts his head up, "that's what I like."

Something in Dean's eyes shift, change. The tension in the room makes Sam's heartbeat ratchet up.

"That all you like, Sammy?" Dean mutters, rubbing at Sam's inner thigh.

No, no it isn't. That's why he leans forward and kisses Dean. It feels like moving past the glass wall he put up between them, it feels like taking the cuffs off his wrists, it's coming home.

"Wait, does that hurt?" he breathes, rocking back.

"Just a little," Dean answers in a rasp, but stands up in a flash.

Standing between his thighs, Dean kisses him intensely, holding his face and his waist. Sam can feel him breathing hard through his nose, gets his hands on Dean's shoulders. He locks his legs around a tapered waist and squirms on the table top when Dean's takes a breather.

"Look at you, good boy," Dean pants, shoves Sam flat to the table and brings his ass to the edge by his thighs.

Weeks of testing boundaries and sexual tension have Sam desperate for Dean's touch. He cries out when that hard cock presses into the crack of his ass and Dean leans over to get his mouth sloppy on Sam's again.

"Goody two-shoes letting me fuck him up, finally," Dean huffs against pink lips.

Arching against the table Sam groans and tries to unbutton his shirt, but Dean tears it open.

"God, that's so fucking hot," he whimpers, spreading his legs farther apart.

Dean laughs breathlessly as he plants open mouthed kisses on Sam's neck and collarbone, letting his hands travel heavy and slow down Sam's sides. He grinds them together and doesn't notice that the table rocks and wobbles with each thrust of his hips. 

"How d'you want it, pretty boy? Wanna get fucked on the table? Or you want it on the bed?" Dean asks into Sam's ear, some of the locks sticking to Sam's flushed face.

He just gets a sobbing moan and big hands clutching the back of his t-shirt. When Dean tries to stand up straight, Sam pulls at him, locking his legs tighter. But Dean notices a necklace around Sam's neck, black string with an amulet that seems all too familiar.

"Dean, please," Sam begs, reaching down to cup him through his jeans, "want it, I want it."

"Alright, where's your lube? Tell me where it is and you can have it," Dean nods, pushing into Sam's palm.

Sam points lazily at his bedroom and Dean is quick to lift him up from the table, carry him as he puts his hands under Dean's shirt. Tries to tilt his hips to get at Dean's dick and suck hickey's into either side of his neck.

Dean hasn't been with anyone since he laid eyes on Sam that day, so he's clean. Couldn't think about the kid without popping a boner immediately.

"You clean?" he asks, tossing Sam on the bed.

"Y-yeah, lube is in the drawer, turn on the lamp," Sam mutters.

He takes off his ruined shirt and gets to work on his belt and slacks when the dim light illuminates half the bed. His favorite white comforter has tiny holes in certain places, allowing the feather to escape. Some still floating down and around him as he pulls his pants down and off.

"Sure you want to do this on your back?" Dean climbs onto the bed with the lube.

Sam nods and hooks his fingers into the elastic of his boxers to tug those off, too, baring himself to Dean.

"Legs so fucking long, spread them, let me see," Dean croons, crawling up to Sam.

He opens up completely and reaches to pull himself apart so Dean can get a good look at his hole. He hiccups out a sob when a dry finger brushes against him, his dick twitching. 

"You can come if you need to take the edge off," Dean grunts, coating his fingers in the cold substance.

Sam shakes his head obediently and lets his head fall back into the pillows when Dean slips his finger inside him. He doesn't want to come yet, he wants to do it on Dean's dick. He's jerked off to this with his vibrator stuffed inside himself, feeling like it still wasn't enough no matter how many times he made himself come. He shakes when a second finger breaches him but he accepts it easily.

Dean takes his swollen length in his hand and strokes him from base to tip loosely, forcing Sam to bite the back of his hand.

"I spent my nights wondering if you'd like this. If you liked to take it while on your back or flipped over on your stomach," Dean whispers, pulling his fingers out and coating a third.

Sam sucks in a breath and lets his hands travel to down to his nipples, rolling and pinching them lightly. 

"I thought about how you'd suck my dick, whether you liked to go slow and tease, or make me lose my load quick," Dean admits while pushing three fingers inside.

"Both, I'd try both," Sam pants, twisting the pebbled peaks harder.

Dean struggles to get his jeans unbuttoned and down to is knees, bringing his briefs down after.

He catches Sam staring down between his legs, licking his lips. He presses in deep and crooks his fingers for his knuckles to brush against Sam's prostate.

Sam yelps and makes a grab for his cock, gripping the base to stop himself from coming. Dean still smirks at the few beads of slick that make it out of his slit.

"I've been thinking about your dick, it's time that it stops being a thought before I finish too fast," Sam growls impatiently.

Dean pulls out gently so he can take all his clothes off, throwing it all to the side of the bed and crawling between Sam's spread legs.

"You know what I really liked thinking about?" Dean mumbles against Sam's mouth.

"What?" Sam asks, thickly, anticipation making him feel like he might explode.

He holds his breath when Dean starts to push inside of him, spreading him open like he spread his legs. He tries not to clamp down around the intruding member but his cock keeps throbbing in time with his heart, and he can't help it. Dean breathes through it with him, closing his eyes and his eyebrows drawing together till he's balls deep.

He takes a shuddering breath and watches Dean's fluttering eyelashes, eyelids shoot open to a glimmering green. He chokes when a shallow thrust is given because, fuck, that's all of him in there. 

"I wondered if you'd come on it, just my dick," Dean says in a ragged voice.

Sam jolts once and nods, cause he will. He is.

Dean holds Sam's hands down to the bed and starts to thrust into him. Once he picks up enough momentum, the bed starts slamming against the wall. 

"Oh shit, oh my fucking shit!" Sam shouts at first, can't even hide his face in his arms like he'd like to when something is too much.

"There we go, noisy one aren't you," Dean purrs with a smug grin from up above.

Sam keeps contracting around him, trying to keep Dean inside, put pressure on his inner walls constantly. He fights the hold, thrashes and arches, cries out because he's gotta come.

Dean hears Sam whimper something, but it gets lost when he shouts again. The kid is something else, cheeks pinked up and his mouth slack.

"What was that? What did you say?" Dean asks between breaths, swiveling his hips.

Dean pulls out and pounds into him steady a few times, forcing Sam to shriek.

"I love the way you fuck me," Sam says in a convulsive gasp.

"Yeah, you do," Dean grunts and takes Sam's arms to pin them to his chest.

The sky outside is starting to get lighter and Dean holds Sam down like that, makes him take him to the hilt. Sam gets fucking loud, then. Throwing his head back and wailing to the ceiling. 

"I'm gonna fucking come on your dick," Sam hiccups, his hands curling into fists.

And he does when Dean pushes in and up. Eyes roll back and Sam pulses out onto his own stomach as Dean slows down some and watches how he spurts harder when Dean thrusts inside.

Cause the kid is fucking magic, coming untouched on his cock, Dean goes off with a gasp, creams him full. He lets go of Sam's arms and rests his head on his shoulder wile they catch their breath.

"I pictured that going a hundred way, but this...wow," Sam says.

Dean chuckles tiredly as he pulls out and rolls over to Sam's right side. They lay in companionable silence until Sam rolls over into him.

"Don't go to work today," Dean mutters.

"I wasn't planning on it," Sam answers.

Dean turns his head when Sam gets up on an elbow to look down at him.

"I need a shower, I feel like a cumdump," Sam's mouth curls up into a smile.

"Kinda just were," Dean snorts and hides his face in the pillow when Sam punches him in the shoulder with a boisterous laugh.

That amulet catches his eye again and he feels like he should remember it.

"Where'd you get that thing from anyway?" he asks, jutting his chin at it.

Sam touches it gingerly, bow lips curling up in a sad smile.

"Bobby and Jody said it's the only thing I had," he shrugs. 

"Only thing you had?" 

"Yeah, when they adopted me," Sam blinks.

**Author's Note:**

> Tumblr: @deantops-sambottoms


End file.
